Deciding to retire at any time depends more on your personal financial readiness than on the calendar year itself. But while there is no one-size-fits-all answer, there are certain indicators to tell if you’re ready to take the leap in 2026.

In this week’s Money Wisdom Question Series, Heath Grossman, CFP® shares five key steps to help you understand whether you’re truly prepared.

1. Your Expected Income Covers Your Expected Expenses

In retirement, your priority shifts from saving and growing your money to generating reliable income to cover your expenses. That income may come from Social Security, pensions, or investment withdrawals. In addition to knowing your income sources, understand your future living expenses. Having a well-crafted income plan can help ensure you have enough to support your lifestyle.

2. You’ve Accounted for Inflation and Health Care Costs

When estimating your future expenses, be sure to factor in inflation. The $5,000 per month you spend today will cost significantly more a decade from now. That’s why your income plan should allow you to give yourself “raises” over time. Rising out-of-pocket medical costs, which tend to increase as you age, are another key consideration.

3. You Have a Tax-Efficient Withdrawal Strategy

A strong withdrawal strategy starts with knowing how much of each withdrawal you’ll keep after taxes. You should know the optimal order to withdraw from taxable, tax-deferred, and tax-free accounts. When and how you take money out these buckets can help minimize your tax liability over the long term.

4. You Have a Clear Vision for Your Lifestyle

Living a fulfilling life in retirement doesn’t happen automatically — you need a plan for how you want to spend your time. Consider activities like traveling, pursuing hobbies, volunteering, or exploring new interests to make these years especially rewarding. Some retirees even choose to work part-time simply because they enjoy staying active and engaged.

5. You’ve Consulted a Financial Advisor

Another way to determine when to retire is to discuss your situation with a retirement planning professional. An advisor can help you build a comprehensive retirement income strategy aligned with your financial goals and desired lifestyle.